There are quite a few shows that you couldn't realistically get new copies of so I don't think any reasonable person would object to trading in used copies of shows. I know there's been a long running debate about used game sales and it has been quite interesting but I think that eliminating the sale of used items is a little too unfair to customers and bit too favourable to publishers. One of the good things about the debate over used games is that companies do seem to be trying to give more value to those who purchase new, it doesn't always work out but at least there's some effort being made to try and create more options and fairer solutions.
I tend to try and buy things new but it's mostly just personal preference. Still, if I didn't buy anything used then I wouldn't have Azumanga Daioh and I might not be the "cute girls doing cute things" fan I am today (hey, it's a good thing... I think).
I think Rui made a really good point about the way people perceive their wealth and disposable income. I know I begrudge every penny I spend on food, clothing and such because I need it to buy anime (I'm probably not joking as much as I should be). A Crunchyroll subscription really isn't that expensive, you'd maybe have to cut back on a couple of your favourite drinks but you'd get a lot in return and you'd be contributing.
As for pirating to buy, I'm not really going to complain too much as long as you stick to it and absolutely avoid anything with a legal streaming option. Ideally everything would have some way to sample it, even if it's only a couple of episodes before you have to pay but since that's not the case I guess I can understand people being cautious. Still, I'm not sure it's exactly acceptable since you'll likely end up funding people who are basically doing nothing but stealing. It's also a little shaky since you have to decide just how much you allow yourself to watch before you're paying for a show. If you watch the whole thing but at the end feel you didn't enjoy it and wouldn't want to own it then I still think it'd be unfair to avoid paying (you could always buy it then sell your copy as used, I suppose).
I wonder who decided to call it "Piracy" anyway, I guess Pirates are technically bad but from a fiction point of view they're also cool. It wouldn't surprise me if some people were at least partly influenced by that, though it's also kind of a sad thought.